You Don't Know Jack
by svenjen
Summary: Ever wonder why Blair ever slept with Jack in the first place? As they try and put their relationship back together again, Blair finally comes clean to Chuck about what really happened that New Years Eve. Definitely CHAIR, with a heap of Jack, Rated M/A.


**You Don't Know Jack!**

**Summary**

Ever wonder why Blair ever slept with Jack in the first place?

As they try and put their relationship back together again, Blair finally comes clean to Chuck about what really happened that New Years Eve.

**Disclaimer:** I still do not own Gossip Girl in any way, shape or form. This piece was created for entertainment only.

**Warning:** **This story is rated a T+ for mature content.**

**XOXO**

After their formidable reconciliation following their little war, Chuck and Blair began trying to put their broken relationship back together again. But it was hard. Certain issues kept cropping up, road blocking any possible progress. Chuck fucking Jenny, for example, continued to be an issue for Blair, as was Blair's involvement was Jack.

Blair was willing to forget the whole Jenny issue. Chuck had, after all, had used many whores before for sexual relief. And in Blair's mind, Jenny was but another dirty whore.

But Chuck just couldn't seem to shake the Jack issue, despite the fact that he had set Blair up. It was beginning to piss her off.

"We need to get past this," Blair pleaded one evening after he had commented about Jack once again.

"I'm sorry, you're right," he admitted. "We've been over this before. Several times! But you know it's a sore spot for me and probably always will be."

"I hate that man," Blair quietly stated as she shook her head recalling all of the grief that Jack had caused them.

"And yet you slept with him once before that night too," Chuck snarled under his breath.

Blair shook her head in dismay. "Must it always come back to that? That's in the past. It's over, ok?" She turned her back on him, hung her head and sighed. "You know how much I love you. You really don't know how difficult it was to go to him."

"I would never doubt your love after you agreed to prostitute yourself out to my uncle for me last spring," Chuck acknowledged. "But the fact is, you still went willingly," he grumbled. He sighed and swallowed the last of his scotch. "So, no, I can't imagine how difficult it must have been," he added sarcastically.

Blair sighed again. She refused to get angry with him. He really didn't get it. And at that moment she decided it was time to come clean. She looked at Chuck as the tears began to pool in her eyes. She forced herself to swallow the lump in her throat and take a deep breath. "You're right. It wasn't difficult…," she admitted in a voice barely louder than a whisper. "It wasn't difficult, because it wasn't the first time I had to whore myself out to him."

Chuck looked at her and blanched. He was shocked. He felt as though she had just slapped him. "What do you mean?" he asked in disbelief as he sat beside her on the side of her bed.

"I think it's time I told you about what really happened that New Years Eve," she said.

Chuck tried to swallowed the panic he felt building in his throat. He wasn't sure if he wanted to hear what she obviously needed to say to him.

Blair turned to him and reached for his hands. "You had been through so much with your father's death and the funeral," she began. "I wanted to be there for you so badly. And then I told you I would stand by you through anything. I really did mean it, Chuck. I, … I told you I loved you, but then you told me, 'Well that's too bad. And then you got in your limo and just left me standing there on the curb. It hurt so much. All I wanted to do was to be there for you. To love you. To help you with your pain. But you left. And then later that night, you showed up in my room. You were so broken."

Chuck nodded his head. He remembered exactly how broken he had been that night. He had needed her desperately then. And she had known how much he needed her. Blair could have turned him away right then for him hurting her earlier. He knew how much he had hurt her again. But she hadn't. Instead she'd wrapped her arms around him and held him tightly against herself. She had comforted and loved him, while he released his pain on her. He had finally fallen asleep in her arms, feeling more safe and loved than he could ever remember feeling in his whole life. He almost believed he could get over his grief if only she could be there for him.

But that belief didn't last. When he awoke the waves of pain began to wash over him again. It was more than he could bear. He just had to get away from it, from the memories, and even from her. He had jotted a quick note and placed it beside her, brushing a soft kiss against her cheek before he left.

"It almost killed me when you left," Blair continued. "It felt like my soul had been ripped right out of my chest. I was sick with worry not knowing if you were alright or if you were maybe even dead. I couldn't eat or sleep. Dorota was so scared for me, she didn't know what to do. I couldn't stop crying. I couldn't function all through December. I didn't even care that it was Christmas, Chuck. I just didn't care about anything else but you anymore. I couldn't stop feeling that I'd lost you forever," she cried as she recalled just how frightened she had been for him.

Chuck squeezed her hands, and looked into her eyes. Her pain made him wince. "I know, Blair," he whispered. "I really am sorry."

"And then Jack showed up after Christmas and I had hope once again," she continued, daring not to stop. She looked down at their entwined hands and took another deep breath. "Lily had asked him to come and take care of Bass business while you were missing. I had to see him, to ask him if he knew were you were," she confessed. "I was desperate to know if you were alright. Surely he would have news of you, I thought."

Blair continued the story as tears began to drip down her cheeks. She squeezed Chuck's hands again gently, causing him to look up at her. Her eyes held his while she continued on.

"At first Jack just brushed me off," she explained. "He wouldn't even acknowledge my presence, let alone give me answers. He wouldn't tell Lily anything either. We both tried." Blair shook her head remembering how very frustrated she had been.

"For the next day or two I constantly sought Jack out and begged him for word of you. He was getting pissed off at my persistence," she relayed. Chuck smiled a little at that. He certainly knew how persistent Blair could be, when she wanted to be. "Finally," Blair continued, "A couple of days before New Years Eve, Jack spoke to me, confirming my worst fears…..."She felt her memory slipping back as she began to explain the events as they unfolded in her mind…

_"Chuck's not doing well, Blair," Jack finally relayed as he shook his head in disgust. "The news is that he's submersed himself in opium and booze, maintaining a state barely above comatose. He's on a suicide run," Jack told her coldly. "And he's not likely to ever come back … He's too far gone," he added as he watched her crumble to the floor before him. "I think it's pathetic, if you ask me," he sneered._

_Blair fell apart. It was her worst nightmare coming true. She had been so afraid that Chuck was hurting himself. He was alone, hurt and now possibly even dieing. She felt what was left of her world collapse around her. She didn't know how she would go on if she lost him. And then she felt Jack's hands on her back, rubbing her shoulders as he attempted to comfort her. _

_"Can't we just go and get him, Jack?" Blair asked through her tears. "We could make him come home. Please," she pleaded. "Maybe it's not too late to get him back."_

_"I don't know where he is," Jack replied. "The information I've been given is just from miscellaneous reports. Chuck is missing. No one knows where he went to after the last report. I'm sorry, Blair. I didn't want to tell you because I knew it would hurt you," he told her. Jack helped her up to her feet and pulled her into a hug, letting her cry against his shoulder. He stroked her on the head for a moment and then leaned down and kissed her hair softly. _

_His touch brought her around. "I…. I need to leave," Blair stated as she pulled away from Jack and bolted to the door. His touch disturbed her and she needed to be alone. She somehow made it back to her family's penthouse where she collapsed numbly onto her bed. She was too stunned for tears. Chuck was gone. _

_Dorota was very concerned. Blair had run into the suite and bolted up the stairs past her without saying a word. The mascara smeared across her puffy face told the maid of her mistress's distress. She finally called Serena, asking her to come and see Blair. "I am worried about Miss Blair," she told her friend. "I think something has happened about Mr. Chuck."_

_Serena had come over a little while later and had spent the night trying to consol Blair and find out what had happened. Blair wouldn't tell her anything for the longest time. Just the thought of verbalizing what Jack had told her was too much to bear. Finally, after hours of Serena just holding her, Blair had simply whispered, "He's not coming back."_

_Blair had remained in her room until New Years Eve. Dorota had repeatedly begged her to get up and go out. The maid was off for a couple of days and was worried about her charge. She finally called Serena again, who promptly popped over to see Blair. _

_After a lot of nagging, Blair promised her persistent friend and her maid that she would get up and go to the party at the Palace that night. She finally got off of her bed, showered and went through the ritual of preparing to go out. She didn't think she could follow through with it. But when Serena showed up to take her, Blair nodded in agreement that she'd go, if only for awhile, to appease her friend. _

_Once at the Palace, however, Blair found that the drinks were going down easy. She hadn't eaten in days and soon found herself somewhat buzzed from all the alcohol she had consumed on an empty stomach. She sat back in her booth and allowed the effects of the alcohol to wash away some of her pain as she watched her friend dance the night away. _

_Before Blair knew what was happening, Jack Bass had slid into the booth and was sitting beside her, looking at her with what appeared to be amusement in his eyes. "Happy New Year," he told her. _

_"Not really, Jack," Blair admitted glumly. She slid out of the booth, attempting to leave him there, but she stumbled over her own feet. Jack's hands quickly grabbed hold of her waist to steady her before she fell. _

_"Thanks," she grumbled as she brushed his hands away from her._

_"I think I should take you home," Jack stated and began to steer her towards the door. Against her better judgement, Blair agreed. She really just wanted to go home._

_Jack loaded her into the limo and sat back watching her with amusement while they made their way to the Waldorf penthouse. "Thanks," she stated as she stepped out of the car once they'd reached her building._

_"I'll see you up," Jack commented as he took her by the elbow to guide her unsteady feet. He escorted Blair into the penthouse and had her sit down on the sofa in the living room. He sat beside her and then turned to her. "So, how are you really doing?" he asked._

_She looked at him in disbelief. "Really, Jack?" she scoffed in disbelief. "How am I doing? How do you think I'm doing?" she asked. "I'm miserable without Chuck, ok. I am so afraid for him and am so sad about never seeing him again. It hurts me so much…..," she cried as fat tears rolled down her face again. She wiped her eyes and covered her face with her hands. "I love him. I'd do anything to have him back."_

_"Hmm," Jack replied with a smirk. "Anything?"_

_Blair nodded her head as she felt a fresh shower of tears erupt. "I just want him back safe," she admitted._

_Jack scooted over closer to Blair and he put his arm around her shoulders. He took a hanky out of his pocket with his other hand, and held it out to her. "Just how badly do you want him back?" he whispered in her ear. _

_Blair lifted her head out of her hands, took the hanky Jack was offering, and wiped her face and eyes. She looked at him in confusion. "Jack," she asked in disbelief. "Do you know where Chuck is?"_

_He offered her another smirk and then caressed the crook of her neck with his hand. "I might," he offered._

_"Tell me. Please," Blair begged as she slid a little further away from him on the couch. He was a little too close and was making her feel uncomfortable. "I need to get him home."_

_Jack slid closer to her again. He took his free hand and brought it to her knee. He squeezed it slightly and looked at her. "Maybe," he said. "But I'm not sure if I want him to come home. Chuck really wants to stay doing what he's doing. He'll kill himself eventually regardless of where he is, you know. There'd be just so much more drama with him here doing it."_

_Blair looked at Jack in shock. The bastard had known where Chuck was all along, she realised. She could not believe that he would allow his own nephew to self destruct and possibly even die all alone in some foreign country. Chuck was still a boy, a child in many ways. Just what kind of monster was this man, she asked herself. And then she felt Jack's hand move from her knee up her thigh a little and she knew what he was asking. She looked at him with a combination of disbelief and disgust. "No!" she said._

_Jack smirked at her and shrugged his shoulders. He then began caressing her thigh once again. "I could bring him home for you, you know," he delivered smoothly. He slipped his other arm from around Blair's shoulders and brought his hand down to stroke along the side of her face. "He'd be safe," he whispered to her. _

_Blair looked at Jack in horror. What he was proposing was both indecent and inhumane. He wanted her to have sex with him, and then he would have Chuck brought home to her. _

_She shook her head again. "Jack, no….. please,,,,," she begged. "There has to be another way. I… I could give you some money," she offered and looked at him desperately._

_Jack laughed at her. "I'm a wealthy man, Blair. I really don't need or want your money." He stroked her thigh a little higher and she winced under his touch. "I guess you need to think about how much you really do want him back. What's Chuck's safety really worth to you?" he asked her smugly. _

_He stood up from the couch and headed over to the bar at the opposite end of the living room. He poured himself some wine and asked her if she wanted some too. When she nodded yes, he grinned and poured her a glass._

_Blair hung her head in defeat, letting the tears fall once again. The thought of Jack even touching her made her brain scream and her body shudder with revulsion. But the thought of losing Chuck was even worse for her. She could not stand the thought of his demise, when there was a possible way of saving him. _

_When Jack passed her the glass, Blair downed the wine in one shot and asked him for another. He passed her his full glass and went to fill the now empty one for himself. He smiled again when he noticed she had finished his glass too. _

_"Easy princess," he cooed to her. "I don't want you too drunk now. That would take all the fun out of things, wouldn't it? And Blair….," he continued. She looked up at him to see what more he could possibly want from her. "You need to stop crying. You need to be a willing participant here or the deal is off," he informed her._

_Blair nodded her head and wiped her eyes once more. She had to be strong, she told herself. If it would save Chuck and bring him home safe to her, she could do it. "When will you bring him home?" she asked in defeat._

_He grinned at her, knowing he had won. He polished off his drink too, now eager to get the party started. "My people can have him on the Bass Jet within 48 hours," he informed her. Jack took the empty wine glass from her hand and set it down on the coffee table. He helped her to stand up._

_Blair could feel her head swim as he took her by the hand and led her to the foot of the stairs. And then she stopped. When Jack turned to look at her questioningly, she asked in a small voice as she bit back the tears that wanted to fall again, "How do I know that you'll bring him home safe to me?"_

_Jack smirked once more. "You'll just have to trust me now, won't you?" he replied._

_She nodded in defeat. He was right. She would have to take his word for it. It didn't really matter, she thought. Without Chuck, she wouldn't be able to go on anyways. She would sleep with his uncle if it meant that he would be returned home, safe to her. _

_Blair recalled the afternoon before the night Chuck had left her. 'I will stand by you through anything,' she had told him. Those words began to play over and over again in her head as they walked up the stairs. 'And why would you do that?' he had asked her. ''Be… because I love you,' she had replied to him. She loved him, and this was the anything she had promised him. She knew there was no other way. _

_At the top of the stairs, Jack hesitated until Blair motioned to him which bedroom was hers. He opened the door and flicked on the light. "Nice," he observed as his eyes travelled over the decor of her room. "I knew you would have good taste." He closed the door behind them and turned to face her. He put his arms around her and pulled her close to him. "Put your arms around me, Blair," he ordered her. She complied. He leaned in and put his lips against her neck. "Hmmm," he moaned as he savoured her neck. "You also taste good," he informed her._

_Jack reached for the zipper at the back of her dress and slid it down her back, raising his hands to her shoulders to pull it down. The dress dropped to her feet. He stepped back to observe Blair in her silk camisole and panties. "Nice," he commented, with approval. _

_Blair ignored his remarks and walked over to turn on a small table lamp that offered only a low shadow of light. She turned off the main light switch in the room. This would be easier in the dark, she thought. She went back over to Jack and began to unbutton his shirt. He smiled and nodded in agreement, leaning in to kiss her lips as she began to undress him._

_She closed her eyes and tried to kiss him back. Blair could feel the effects of the wine as it interacted with the alcohol she'd had earlier. It started to fuzz her head up. Good, she thought, it would be better that way. She noticed that Jack was wearing cologne that was very similar to one that Chuck often wore. If she tried hard enough, she thought in her drunken mind, she could almost imagine it was Chuck, and not Jack, who she was with. There were other similarities between them too, she noticed. They had a similar height and build, although Jack had a few more muscles than Chuck did. Jack's hair was also a similar length and texture to Chuck's, she realised as she ran her fingers through it. She smiled. In the dark with my eyes closed, she told herself, it's easy to see someone else if you need to. So in her mind, it would be Chuck she was with tonight, and not Jack. She smiled to herself. If she could stay focused, it might work for her._

_And with that belief, Blair's mind settled and she gave herself over to the alcohol and the belief that it was Chuck she was with. Once that notion took hold in her brain, she became an extremely eager participant in the activity that was unfolding in her room. It had been, after all, months since she had held Chuck in her arms. It had been also been months since she had felt the pleasure of a man's body against her own. _

_She was doing such a fine job of pretending and had so much pent up desire in her from being neglected for so long, that she actually couldn't help but respond to Jack's administrations on her. She was so eager, in fact, that it completely startled Jack. He had figured Blair would be a cold fish to him, a prude, a complete non-participant. But what he got once she got started, was beyond his wildest dreams. _

_When she closed her eyes it was Chuck who was holding her, kissing her, and loving her body, not Jack. She found that when he held her, the pain of missing Chuck was almost gone. She felt relief both emotionally and physically as things progressed. And she was desperate to feel closeness and release. As long as she kept her eyes closed and pretended it was Chuck, Blair told herself, then it wouldn't count. So in Blair's mind it really was Chuck, and not Jack that she was with. And as her mind slipped further into the fantasy, she found her own passion mounting. Things began to progress rapidly from that point on._

_Before she knew it, they were in her bed, between her sheets. Jack was taking her under clothes off, and she was eagerly letting him. She moaned as he began to stroke her wet center. She reached down and felt his hardness against her thigh. Somewhere, he had lost his pants. She couldn't recall if it was her or him who had taken them off. She stroked his length, noting with a smile, that he wasn't nearly as big as his nephew was. _

_Blair shook her head and tried to refocus on what was happening. She dared not think of Jack at all, lest she lose her willpower and reserve. It was Chuck she was with, she convinced herself again. _

_Jack ran his mouth along her throat and down onto her small, but pert breasts, enjoying their youthful fullness. "Beautiful," he commented. _

_Blair slid her hands up over his back and ass, gently raking her nails against Jack's fevered skin. She was becoming somewhat impatient with his pathetic attempt at foreplay. She finally reached down and took him in her hands, slowly guiding him into her. She arched her back and groaned as he slid into her heated core. _

_Jack moaned at the sensation as he tried to fill her. He eagerly began pounding into her. _

_He wasn't big enough to do much for her. "Deeper," she hissed and she slid her legs up over his shoulders, egging him into her center deeper. But she found that she still wanted more penetration than he was providing. "Harder," she demanded. She needed the sensation of being filled to help her keep the scenario alive in her mind._

_Jack groaned as he tried his best to comply with Blair's request, He slammed himself into her as hard and as fast as he was capable of. She was so tight, and so beautiful that he was already feeling like he could cum any moment. Her responsive body was more than he could have ever asked for._

_Bair felt Jack's body begin to clench and realised that he was getting close already. Again, she smirked at his poor stamina. She reached down and began to circle her fingers around her own swollen nub, needing the release she knew Jack was incapable of providing her. As her walls began to flutter around him, Jack erupted with a moan, biting into her shoulder as her waves milked him dry. He whimpered when she finally finished contracting around him, and he collapsed against her chest. He was completely spent. _

_"Fuck!" he stated after he had puffed and panted for a few minutes. "That was incredible," he admitted as he kissed her neck. He finally rolled off of her and flipped over onto his back. _

_A few moments later, Blair sat up and slowly got off the bed. She turned to look at Jack as she headed into her bathroom. "I expect to see Chuck home safely in a couple of days, Jack," she informed him. "You can see yourself out."_

_Blair began to run the shower and then collapsed in tears at the foot of the toilet, her body shaking uncontrollably. Now that it was over, reality set back in. She had never felt so filthy and so utterly disgusted with herself in her entire life. Slowly she stuck her fingers down the back of her throat, easily gagging with the taste of Jack still on her fingers. She quickly emptied the contents of her stomach until there was nothing left for her to possibly vomit. It was the first time she had relapsed in months, but she felt the occasion warranted it._

_When she regained her strength, Blair quickly brushed her teeth and got into the shower. She turned the water's temperature up as hot as she could stand it, almost to near scalding. She took a scrub brush and began to soap and scour herself from head to toe, desperately trying to remove every last bit of Jack from her body. _

_While she scrubbed, Blair cried and cried. The tears wouldn't stop. She kept repeating her promise to Chuck in her mind, trying to justify her earlier actions. 'I will stand by you through anything,' and 'Because I love you,' she told herself over and over again until she finally began to feel clean again. _

_Finally, she shut off the water and briskly dried off her tender skin. She slowly stuck her head out of the bathroom door, peaking to see if Jack was still in her room. She sighed with relief when she spotted her empty bed. She quickly threw on her most conservative cotton nightgown and grabbed her favourite Teddy-bear from the back of her closet. She would need something to hold tonight! She tore the now soiled bedding off of her mattress, and wrapped herself up in the down quilt she kept neatly folded on a chair in her room. She finally turned off her bedside table lamp and climbed into bed as the painful sobs she'd been holding, began to erupt from deep within her._

_Jack was just about to head down the stairs when he heard Blair come out of her bathroom. He paused for a minute, holding the railing. He smiled at the memory of her panting beneath him just a short time ago. He considered turning around and going back into her room again. Perhaps she'd be game for another round, he thought. _

_But then he heard the almost animal like sobs erupt from deep within Blair as she crawled into her bed. It made him shudder and he quickly headed down the stairs, into the elevator and out into the night to his waiting limo. He stopped short for a moment when he heard the confusing sound of horns and whistles begin to blare around him. "Happy New Year," somebody shouted from somewhere in the shadows. Of course, he smirked. Happy New Year! He chuckled to himself. Yes, it certainly was!_

_Approximately 52 hours later, Jack hauled his inebriated nephew from the limo and dragged him into hotel. _

Chuck sat in complete shock as Blair relayed the painful details of her story to him through her tears. To say he was shaken was an understatement. He was absolutely floored! He reached out and pulled Blair into his arms as the final details were brought forth. He could feel his own tears start to fall.

"I never wanted you to know about it, Chuck," she admitted. "But you have to understand. I just wanted to forget it ever happened. Jack promised me he'd find you. He promised me he'd bring you home safe. He promised me you were going to be ok. I could see no other way to get you back. I really believed I had no other choice. So I slept with Jack in exchange for your safety. I would have done anything for you to get you home safe. And I did," she sobbed as Chuck stroked her back.

"And that's why I knew I could do it again," Blair admitted. "The Empire meant everything to you. You were falling apart and it scared me. I was so afraid of losing you again, so I chose to go to Jack just like I had done before. I guess if you've whored yourself out once, it's easy enough to do again," she cried into his chest. "So, you're right about that, ok? But you needed to know why I did what I felt I had to do. So, please, Chuck….," she concluded, "I don't want to hear about what I did or what I was willing to do with Jack. I know. I lived it. And I live it over again every time it gets brought up. I don't want to remember it any more, ok? But I wouldn't change any of it, if it means that you are here with me today. But if we're ever going to move forward in this relationship, you have to let it go and we have to move on; just like I'm trying to do."

Chuck continued to hold her in his arms until her sobs finally stopped. "I'm so sorry, Blair," he cried, "I am so sorry for what I put you through."

"It's alright. You had no idea," she acknowledged. "I just want to move past it now, ok?"

He kissed her head. "Ok, I promise," he told her. He would never mention Jack to her again, but he knew her story would probably haunt him for the rest of his life. "I love you so much," he told her.

"I love you too," she sighed. It was over and she could put it to rest. Now, she was sure, they could finally move on. Chuck and Blair would be ok. "Thank-you," she whispered against his heart.

Fin.

**XOXO**

**A/N:** This was a tough little story to write…. The whole New Year's incident with Jack just drives me nuts. I can not see Blair sleeping with him for the hell of it. In my mind, something had to have happened. I know I have touched on this in a couple of my other stories… either with Jack drugging or raping her in some way or another. But this situation makes the most sense to me. It is what I imagine happened in my own mind and helps tie that Empire thing together too.

**Please tell me what you think. This was my first attempt at a one shot! How'd I do?**


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